1. Field of the Invention.
This invention relates to the chemical compounds 1,1,4,4-tetrakis(trifluoromethyl)butan-1,4-diol and 1,1-bis(trifluoromethyl) propanol-1 and to methods for preparing them. 2. Description of the Prior Art.
.alpha., .omega. Glycols have found considerable use in the chemical arts. For example, 1,4-butandiol, made by the hydrolysis of tetrahydrofuran or from a reaction between acetylene and formaldehyde, is used in the production of Perlon U (a polyurethan fiber) and in the production of .gamma.-butyrolactone.
Heavily fluorinated organic compounds have also found considerable use. As examples, consider the fluorinated compounds well known as the freons and polytetrafluoroethylene (Teflon).
Accordingly, in experiments leading to this invention, it was an objective to prepare a multifunctional alcohol (.alpha., .omega. glcyol) which could be used in the production of polyurethans and which was heavily fluorinated to take advantage of the oxidation resistant water repellant characteristics known to be imparted by fluorine. In preparing the multifunctional alcohol, a monofunctional alcohol, 1,1-bis(trifluoromethyl) propanol-1, was found to be a valuable side product. Insofar as is known by the inventors neither 1,1,4,4-tetrakis(trifluoromethyl) butan-1,4-diol nor 1,1-bis(trifluoromethyl)propanol-1 were ever prepared prior to the preparation described herein.
The most pertinant prior art known of by the inventors is an article entitled The Free-Radical Chemistry of Fluoro Ketones. I. Reaction with Saturated Substrates, E. G. Howard, P. B. Sargeant, and C. G. Krespan, J. Amer. Chem. Soc., 89, 1422 (1967). In this article, Howard et al describe the reaction of various materials with hexafluoroacetone. Among the materials reacted with hexafluoroacetone are n-butane and isobutane.
To react n-butane with hexafluoroacetone, Howard et al dissolved n-butane (a gas to room temperature) and hexafluoroacetone in CFCl.sub.2 CF.sub.2 Cl and irradiated the solution with ultraviolet light from a mercury light. Their analysis showed that they had abtained some 2:1 hexafluoroacetone-n-butane adduct.
To react isobutane with hexafluoroacetone, Howard et al dissolved the two materials in CFCl.sub.2 CF.sub.2 Cl and irradiated the solution with ultraviolet light from a mercury light in a manner similar to that used in the n-butane-hexafluoroacetone reaction except that irradiation was carried out for less time (2 days in the latter case as opposed to 5 days in the n-butane-hexafluoroacetone case). Their analysis indicated that perfluoropinacol and 1,1,1-trifluoromethyl-2-hydroxy-4-methyl-4-pentene were the major products obtained.